Benzyl 3,4,6-tri-O-benzyl-α-D-galactopyranoside | 53929-30-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Benzyl 3,4,6-tri-O-benzyl-α-D-galactopyranoside
• 英文别名: (2S,3R,4R,5S,6R)-2,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-ol
• CAS: 53929-30-9
• 化学式: C₃₄H₃₆O₆
• 分子量: 540.656
• InChiKey: AFHZEIVSXDXEMO-RUOAZZEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  40
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  Dimethyl-(1,1,2-trimethyl-propyl)-((3R,4S,5S,6R)-2,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-silane 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以45%的产率得到苄基3,4,6-三-O-苄基吡喃己糖苷
  参考文献：
  名称：

  Silyl Group Migration in 1-O-Silyl Protected Sugars-Convenient Synthesis of 2-O-Unprotected Sugars

  摘要：

  Reaction of 2-O-unprotected 1-O-silyl-protected D-glucose and D-galactose derivatives 5a-d with benzyl bromide in the presence of sodium hydride as the base afforded 1-O-benzyl 2-O-silyl derivatives 6a alpha/beta - 6d alpha/beta. Thus, prior to anomeric O-benzylation, trans-1,2-silyl group migration takes place. Ensuing removal of the 2-O-silyl group furnishes 2-O-unprotected compounds 8a alpha/beta - 8d alpha/beta, which are useful building blocks. More prone to 1-O-silyl group migration is mannose as shown for derivatives of 4,6-O-benzylidene-D-mannose 9. Cis-1,2- and cis-2,3-silyl group migrations affording compounds 15 and 13 were already observed on deacetylation of the thexyldimethylsilyl 2,3-di-O-acetyl derivative 12 beta under Zemplen conditions.

  DOI：

  10.1080/07328309608005442

文献信息

• Procédé de synthèse organique d'oligosaccharides, correspondant à des fragments de muco-polysaccharides naturels, nouveaux oligosaccharides obtenus et leurs applications biologiques
  申请人：D.R.O.P.I.C. (Société Civile)

  公开号：EP0084999A1

  公开（公告）日：1983-08-03

  Procédé de synthèse organique d'oligosaccharides constituant ou correspondant à des fragments de muco-polysaccharides acides dans lequel on fait réagir deux composés constitués ou terminés respectivement par des motifs de structure sucre aminé et des motifs de structure acide uronique. Ces motifs étant substitués spécifiquement. Ce procédé conduit à des oligosaccharides utilisables notamment en thérapeutique.

  构成或对应于酸性粘多糖片段的低聚糖的有机合成工艺，其中两种分别由氨基糖结构单元和尿酸结构单元构成或终止的化合物发生反应。这些单元被特别取代。 这一过程产生的寡糖尤其可用于治疗。
• Synthesis and chromatographic properties of isomeric O-β-d-galactopyranosyl-d-galactoses, and of diastereo-isomers of 3,4-O- and 4,6-O-(1-carboxyethylidene)-d-galactose
  作者：José D. Fontana、José H. Duarte、Marcello Iacomini、Philip A.J. Gorin

  DOI：10.1016/s0008-6215(00)81792-9

  日期：1982.10
• US4818816A
  申请人：——

  公开号：US4818816A

  公开（公告）日：1989-04-04
• Silyl Group Migration in 1-<i>O</i>-Silyl Protected Sugars-Convenient Synthesis of 2-<i>O</i>-Unprotected Sugars
  作者：José M. Lassaletta、Michaela Meichle、Sven Weiler、Richard R. Schmidt

  DOI：10.1080/07328309608005442

  日期：1996.2

  Reaction of 2-O-unprotected 1-O-silyl-protected D-glucose and D-galactose derivatives 5a-d with benzyl bromide in the presence of sodium hydride as the base afforded 1-O-benzyl 2-O-silyl derivatives 6a alpha/beta - 6d alpha/beta. Thus, prior to anomeric O-benzylation, trans-1,2-silyl group migration takes place. Ensuing removal of the 2-O-silyl group furnishes 2-O-unprotected compounds 8a alpha/beta - 8d alpha/beta, which are useful building blocks. More prone to 1-O-silyl group migration is mannose as shown for derivatives of 4,6-O-benzylidene-D-mannose 9. Cis-1,2- and cis-2,3-silyl group migrations affording compounds 15 and 13 were already observed on deacetylation of the thexyldimethylsilyl 2,3-di-O-acetyl derivative 12 beta under Zemplen conditions.